title: A one-pot enzymatic approach to the O-fluoroglucoside of N-methylanthranilate.
abstract: In connection with prospective (18)F-PET imaging studies, the potential for enzymatic synthesis of fluorine-labelled glycosides of small molecules was investigated. Approaches to the enzymatic synthesis of anomeric phosphates of d-gluco-configured fluorosugars proved ineffective. In contrast, starting in the d-galacto series and relying on the consecutive action of Escherichia coli galactokinase (GalK), galactose-1-phosphate uridylyltransferase (GalPUT), uridine-5'-diphosphogalactose 4-epimerase (GalE) and oat root glucosyltransferase (SAD10), a quick and effective synthesis of 6-deoxy-6-fluoro-d-glucosyl N-methylanthranilate ester was achieved.
authors.affiliation: Laboratory of Bioorganic Chemistry and Crystallography, Faculty of Science and Technology, Free University of Bolzano, Piazza Università 5, 39100 Bolzano, Italy. lorenzo.caputi@jic.ac.uk
authors.forename: Lorenzo
authors.initials: L
authors.lastname: Caputi
authors.forename: Martin
authors.initials: M
authors.lastname: Rejzek
authors.forename: Thomas
authors.initials: T
authors.lastname: Louveau
authors.forename: Ellis C
authors.initials: EC
authors.lastname: O'Neill
authors.forename: Lionel
authors.initials: L
authors.lastname: Hill
authors.forename: Anne
authors.initials: A
authors.lastname: Osbourn
authors.forename: Robert A
authors.initials: RA
authors.lastname: Field
mesh_terms: D018554:Avena / Q000201:enzymology; D004926:Escherichia coli / Q000201:enzymology; D029968:Escherichia coli Proteins / Q000378:metabolism*; D005686:Galactokinase / Q000378:metabolism*; D005960:Glucosides / Q000737:chemistry* / Q000378:metabolism; D005964:Glucosyltransferases / Q000378:metabolism*; D010940:Plant Proteins / Q000378:metabolism*; D005694:UTP-Hexose-1-Phosphate Uridylyltransferase / Q000378:metabolism*; D062367:ortho-Aminobenzoates / Q000737:chemistry* / Q000378:metabolism*
chemical_list: C586293:6-deoxy-6-fluoro-D-glucosyl N-methylanthranilate ester; D029968:Escherichia coli Proteins; D005960:Glucosides; D010940:Plant Proteins; D062367:ortho-Aminobenzoates; C031385:anthranilic acid; D005964:Glucosyltransferases; D005686:Galactokinase; D005694:UTP-Hexose-1-Phosphate Uridylyltransferase
keywords: Biotransformation; Fluorosugar; Glucosyltransferase; Natural product; Sugar nucleotide